Patent GB-602239-A (GB)
Title: Improvements in or relating to lubricants, waxes and other hydrocarbon or substituted hydrocarbon products
IPC: D01H5/06
Filed: 1944-10-12
Abstract: High molecular weight viscous liquid or solid hydrocarbon or substituted hydrocarbon products are plasticised or softened by adding thereto a polyester prepared from the reaction product of a dibasic organic acid and a dihydric alcohol, either one of these reactants having from 15 to 50 and the other from 2 to 50 carbon atoms per molecule.  In the case of liquid lubricating oils the effect of the addition of the polyester is to increase the viscosity index while in the case of very heavy lubricating oils a grease is formed by the addition of the polyester.  The polyester may be added to manufactured lubricating greases and acts as a stringiness agent. In the case of paraffin wax the effect of the addition of the polyester is to destroy its brittleness and to make it flexible.  The dibasic organic acid from which the polyester is prepared may be dimerised linoleic acid, octadecadienoic acid or an acid having the general formula HOOC-CHR-(CH2)n-COOH where R is an alkyl radicle and n is an integer greater than 1.  If desired, the iodine-number of the dilinoleic acid may be reduced by hydrogenation before reaction with the dihydric alcohol.  The dihydric alcohol may be ethylene glycol, propylene glycol, butylene glycol, pentandiol, 2-methyl-2,4-pentandiol, 12-hydroxy stearyl alcohol or other products formed by hydrogenation of castor oil or dimerised linoleic acid. Alternatively, the dihydric alcohol may be one having the general formula OH-CH2CHR-CO-(CH2)n-OH where R is an alkyl radicle and n is an integer greater than 1. Either or both of the dibasic organic acid and the dihydric alcohol may have the following characteristics: they may be saturated or unsaturated, they may be aliphatic compounds or they may contain alkyl, aryl or inorganic substituents, including halogens, oxygen, sulphur or metals, or they may have aromatic substituents in the linear chain between the terminal groups or in side-chains on the chain between the terminal groups.  Where the polyester is unsaturated, it may be treated with chlorine or other halogen, with sulphur chloride or with oxygen to reduce its unsaturation and to render it suitable for addition to a lubricant to improve the extreme pressure properties of the latter.  This is especially valuable with greases and heavy oils suitable for lubricants in which a substantial percentage of chlorine, sulphur, oxygen or phosphorus can be incorporated.  In the case of lubricating compositions, additional ingredients may be incorporated, particularly pour-point depressants, oxidation inhibitors, oiliness agents such as tri-ortho-cresyl phosphate, sludge-dispersing agents such as the condensation product of chlorinated wax and naphthalene, mutual solvents such as high molecular weight liquid alcohols, and dyes.  In the examples: (i) the polyester prepared by the glycolysis of dimerised methyl linoleate with ethylene glycol is added to (a) mineral lubricating oil with or without the barium salt of an alkyl phenol sulphide known as Paronox 56 (the word "Paronox" being a Registered Trade Mark), (b) lubricating grease containing mineral oil and calcium hog fat soap and (c) paraffin wax and (ii) the polyester by esterifying dilinoleic acid with decamethylene glycol is added to Winkler gas oil to produce a lubricating oil.  Specifications 470,580 and 586,871 are referred to.ALSO:High molecular weight viscous liquid or solid hydrocarbon or substituted hydrocarbon products are plasticised or softened by adding thereto a polyester prepared from the reaction product of a dibasic organic acid and a dihydric alcohol, either one of these reactants having from 15 to 20 and the other from 2 to 50 carbon atoms per molecule.  Hydrocarbon and substituted hydrocarbon products to which the polyesters may be added include lubricating oils, lubricating greases, paraffin wax, asphalts, natural rubber and synthetic rubbers such as polybutadiene, the copolymer of butadiene with styrene, the copolymer of butadiene with acryloritrile, and polychloroprene.  The dibasic organic acid from which the polyester is prepared may be dimerised linoleic acid octadecadienoic acid or an acid having the general formula HOOC-CHR-(CH2)n-COOH where R is an alkyl radicle and n is an integer greater than 1.  If desired, the iodine number of the dilinoleic acid may be reduced by hydrogenation before reaction with the dihydric alcohol.  The dihydric alcohol may be ethylene glycol, propylene glycol, butylene glycol, pentandiol, 2-methyl-2,4-pentandiol, 12-hydroxy stearyl alcohol or other products formed by hydrogenation of castor oil or dimerised linoleic acid.  Alternatively the dihydric alcohol may be one having the general formula OH-CH2-CHR-CO-(CH2)n-OH where R is an alkyl radicle and n is an integer greater than 1. Either or both of the dibasic organic acid and the dihydric alcohol may have the following characteristics: they may be saturated or unsaturated, they may be aliphatic compounds or they may contain alkyl, aryl or inorganic substituents, including halogens, oxygen, sulphur or metals, or they may have aromatic substituents in the linear chain between the terminal groups or in side chains on the chain between the terminal groups.  Where the polyester is unsaturated it may be treated with chlorine or other halogen, with sulphur chloride or with oxygen to reduce its unsaturation.  In an example, soybean oil is subjected to alcoholysis with methanol in the presence of sodium methylate.  The methyl esters of soybean oil fatty acids are dimerised by heating in presence of active clay, anthraquinone or BF3.  The methyl ester of dilinoleic acid is separated and subjected to glycolysis with ethylene glycol in the presence of p-toluenesulphonic acid.  The resulting product is the polyester of ethylene glycol and dilinoleic acid and this polyester is added to mineral lubricating oil, lubricating grease or paraffin wax.  In another example, dilinoleic acid is esterified with decamethylene glycol and the polyester thus obtained is added to Winkler gas oil. Specifications 470,580 and 586,871 are referred to.ALSO:High molecular weight viscous liquid or solid hydrocarbon or substituted hydrocarbon products are plasticized or softened by adding thereto a polyester prepared from the reaction product of a dibasic organic acid and a dihydric alcohol, either one of these reactants having from 15 to 50 and the other from 2 to 50 carbon atoms per molecule.  The dibasic organic acid from which the polyester is prepared may be dimerised linoleic acid, octadecadienoic acid or an acid having the general formula HOOC-CHR-(CH2)n-COOH where R is an alkyl radicle and n is an integer greater than 1.  If desired the iodine number of the dilinoleic acid may be reduced by hydrogenation before reaction with the dihydric alcohol.  The dihydric alcohol may be ethylene glycol, propylene glycol, butylene glycol, pentandiol, 2-methyl-2, 4-pentandiol, 12-hydroxy stearyl alcohol or other products formed by hydrogenation of castor oil or dimerised linoleic acid.  Alternatively the dihydric alcohol may be one having the general formula OH-CH2-CHR-CO-(CH2)n-OH where R is an alkyl radicle and n is an integer greater than 1.  Either or both of the dibasic organic acid and the dihydric alcohol may have the following characteristics: they may be saturated or unsaturated, they may be aliphatic compounds or they may contain alkyl, aryl or inorganic substituents including halogens, oxygen, sulphur or metals, or they may have aromatic substituents in the linear chain between the terminal groups or in side chains on the chain between the terminal groups.  In an example soybean oil is subjected to alcoholysis with methanol in the presence of sodium methylate. The methyl esters of soybean oil fatty acids are dimerised by heating in presence of active clay, anthraquinone or BF3. The methyl ester of dilinoleic acid is separated and subjected to glycolysis with ethylene glycol in the presence of p-toluene-sulphonic acid.  The resulting product is the polyester of ethylene glycol and dilinoleic acid and this polyester is added to mineral lubricating oil, lubricating grease or paraffin wax.  In another example, dilinoleic acid is esterified with decamethylene glycol and the polyester thus obtained is added to Winkler gas oil.  Specifications 470,580 and 586,871 are referred to.ALSO:High molecular weight viscous liquid or solid hydrocarbon or substituted hydrocarbon products are plasticised or softened by adding thereto a polyester prepared from the reaction product of a dibasic organic acid and a dihydric alcohol, either one of these reactants having from 15 to 50 and the other from 2 to 50 carbon atoms per molecule.  Hydrocarbon and substituted hydrocarbon products to which the polyesters may be added include asphalts, natural rubber and synthetic rubbers such as polybutadiene, the copolymer of butadiene with styrene, the copolymer of butadiene with acrylonitrile, and polychloroprene.  The dibasic organic acid from which the polyester is prepared may be dimerised linoleic acid, octadecadienoic acid or an acid having the general formula HOOC-CHR-(CH2)n-COOH where R is an alkyl radicle an n is an integer greater than 1.  If desired the iodine number of the dilinoleic acid may be reduced by hydrogenation before reaction with the dihydric alcohol.  The dihydric alcohol may be ethylene glycol, propylene glycol, butylene glycol, pentandiol, 2-methyl-2, 4-pentandiol, 12-hydroxy stearyl alcohol or other products formed by hydrogenation of castor oil or dimerised linoleic acid.  Alternatively the dihydric alcohol may be one having the general formula OH-CH2-CHR-CO-(CH2)n-OH where R is an alkyl radicle and n is an integer greater than 1. Either or both of the dibasic organic acid and the dihydric alcohol may have the following characteristics: they may be saturated or unsaturated, they may be aliphatic compounds or the